Sabrina DeVito: Banking Executive to Entrepreneur and Freedom Mentor

"I’ll write the check, but only if you hire Sabrina."

In 2011, I was trying to raise $2.5M in venture capital to launch and scale Careerminds.
 
One of my lead investors, a former banking executive, had Sabrina as his one non-negotiable condition for funding my company.

I hadn't even met her yet!

At the time, Sabrina DeVito was a banking executive.
 
She had spent decades in the structured, high-stakes world of financial services. On paper, it looked like a massive risk for her to leave the "safety" of corporate to become Employee #3 at a scrappy HR tech startup.

But Sabrina thrives in the messy, build-it-from-scratch phased companies.
 
We met and she was ready to "Clock Out" of banking to build a virtual outplacement platform together.

So, in the Spring of 2011, Sabrina joined Careerminds to lead sales and marketing.

Then something unexpected happened.

A year in, my board of directors asked me to step aside as CEO.

They wanted Sabrina to take over.

I remember the lunch at TGI Friday's where we discussed announcing to the team that Sabrina was now CEO. I would be Chief Product Officer instead.

It was one of the most uncomfortable moments of my career.

But it taught me something I carry to this day: sometimes you must scaffold sideways to build up.

Sabrina ran the company for a year.
 
Then left to join a banking startup.

Which is when I returned as CEO.

We're still dear friends today, 15 years later.

Best of all, Sabrina is my latest guest on the Clocking Out podcast!

What you’ll hear in this episode:
✔️ Why Sabrina moved every 5 years early in her career (and how she knew when it was time)
✔️ How she navigated being the only female executive at Best Egg
✔️ The moment she felt "the itch" and started planning her exit while still employed
✔️ Why she now runs a "portfolio career"
✔️ The uncomfortable dynamics of that Friday's lunch - from both our perspectives

Today, Sabrina is writing her next chapter with Second Careers and Find My Chapter 3, helping people pivot, extend, or restart their careers.

This episode was truly one of the most personal & heartfelt conversations on Clocking Out.

Listen here: https://lnkd.in/eJD7Hzda